Dying Into Life

You have already died a hundred times. And you will need to die hundreds more before you leave this world.

As I reflected recently, one of the greatest casualties of the modern project to sanitize the world has been our understanding of death. There is much to say about our pathological relationship with our inevitable physical end—our “great death” we might call it—but I’ll save that for later reflections. Instead, I will focus here on the “little deaths” that define our lives and work and happiness. (La petite mort has referred to orgasmic experiences, sexual and otherwise, over the centuries but, no, they aren’t the focus today either).

I ask many questions as a coach, as a friend, and as a seeker trying to understand my mind and this life we have all been called into. But perhaps the most important question I often ask is: what do you need to let die?

Regardless of our worldview—atheist or Christian, Buddhist or Jedi—we all recognize that life is a constant cycle of death and rebirth. We see it in the changing of seasons. We experience it in in the turnover of restaurants in our neighborhoods. We read about it on a cosmic scale in the formation and collapse of stars.

And yet somehow we struggle to apply this reality to the details of our own lives.

One of the greatest tricks our minds play is to convince us that we are an unbroken continuum. Unchallenged, my mind tells me that I am the same “Oliver” as the curious 6-year-old boy playing in the woods of Western Massachusetts or the 26-year-old globetrotter desperate to prove himself to a father who had just died. But those Olivers are dead. Every cell that formed that care-free boy has died or evolved. He is an echo, a ghost, shaping this present version of myself, but no more than my physically dead father and mother who I also still carry with me. This Oliver sitting here at my desk will soon die and, if I am fortunate enough that my body still breathes, a new version will emerge.

So it is with everything else in our lives. Jobs, homes, friends, lovers enter our lives, capture our hearts, and then die and transform into new versions of themselves.  Yet we can often only see them as they once were. Witnessing them fully as they are now requires recognizing that their previous manifestations have died, which requires recognizing that that all of this—that job, that company, that child, this body and mind—will also die.

And so we cling and cling and cling. Cling to corpses.

Live and Let Die

Much of the struggle I see in myself and in the leaders and friends I support arises from failure to embrace these little deaths. This is most apparent in start-up companies, which go through rapid and intense cycles of death and rebirth. Many founders I coach know they have to make major changes: let go of the detailed operation of the company or move a co-founder or early colleague out of their role. But they resist, tell themselves stories about why the timing isn’t right or the potential damage is too great. The company suffers, snarled in a kind of arrested development.

They are clinging to a corpse. The early days of the company were hard, but they loved the camaraderie of walking through that fire with their co-founders, the feeling of shaping every detail of this beautiful new thing they were creating like Michelangelo chiseling away at marble. But that early company is dead. The new, evolved company no longer needs the founder to shape—or even see—its details. It needs leaders with skills and experiences the co-founder doesn’t have.

We’ve all witnessed the harms that clinging can cause. Sometimes they are small and absurd: think of the middle-aged man who bellows as he relives his glory days on the recreational basketball court or those who party at their college long after they graduate. But clinging can also wreck our companies, our relationships, our lives.

Trauma is a form of clinging. We clutch the past versions of ourselves in the hope that the corpse will be a type of armor, protecting us from being hurt in the same way again. Parents clinging to their wounded child selves in turn wound their children. Clinging, micromanaging leaders make their teams miserable and drive their organizations into the ground.

We cling out of fear, fear of the pain within the little death, fear that embracing any loss within the job or relationship will mean embracing all loss—that we will be utterly alone and unsafe.

But in one of the harder and crueler of life’s many paradoxes, we only reach the life we long for when we embrace death. Clinging creates the hells we fear. We are fired because we clung to the way the job or company once was. Our spouse or friend pushes us further away because we cling to their older, dead selves and our own.

If we instead surrender to the death, something beautiful can be reborn from the ashes. Sometimes these rebirths occur within the same form. Embracing the death of our spouse’s previous self allows us to witness all there is to love about who they are now, strengthening our marriage. Embracing the death of your early company allows you to find joy in what it needs from you now and change how you lead.

Sometimes these rebirths require new forms. We must leave jobs, close companies, end relationships. We suffer as we do, but then new jobs and new relationships enter our lives, ones that are often truer to who we are now. Birth is hard—messy, bloody, painful. And yet we keep having children.

I have deeply loved two jobs in my life. Leaving each was agonizing, tossing me into a dark, bottomless depression. Friends and colleagues were confused by my decision, believing me to be thriving on a prestigious path. They did not know what those Olivers intuitively sensed: that I had died and the new version of myself was called to different work. The months following my acceptance of the death were a type of bardo, a confusing and painful period in which I cursed and doubted my decision and was tempted to jump at any job that would stop my suffering. But I waited, and eventually the rebirth came. I sit here immensely grateful to those past selves and how their courage and patience gifted me the joy and purpose I feel.

Witnessing Until Rebirth

And I will die again.

Even now I sit here with corpses I haven’t fully released. If this is what our lives are, how can we get better at embracing these never-ending deaths? How can we allow ourselves to be reborn faster and more fully?

I am no master (see corpses above), but I’ve come to believe the answer lies in the art of grieving. Our ancestors understood these cycles, built rituals around them, wove them so deeply into their lives that aspects of their entire consciousness would seem alien to many of us moderns (for a wild tumble down that rabbit hole, spend some time with The Emerald podcast). They constructed elaborate reminders of death and rebirth; we gorge ourselves on presents and hide some painted eggs.

Our modern WEIRD culture sucks at grieving. We fear all forms of death so much that we bury ourselves in frenzied activity and entertainment. We can’t mourn jobs because we start intense new jobs the day after we leave. We can’t mourn beloved homes because we are working nonstop through the move and devote our threadbare attention to selecting the perfect curtains for our shiny new home. We can’t mourn the colleague who has left because there is just so much to do. We run and run, and the corpses pile up behind us until their weight drags us to a halt. Anybody who has experienced a physical or mental collapse knows this intimately.

In some ways, my role as a coach is like that of a chaplain. I help people recognize what has died within their lives and their organizations. And then I sit with them as they begin to mourn, witnessing their pain and the love from which it flows. Once the tears flow, sometimes literally, they can begin taking the slow, hard steps towards rebirth. I am honored to play that role, but it saddens me to think of how few people in this age have that support.

We aren’t meant to do this alone.

That simple statement is so important and so lost in our culture that it bears repeating: you aren’t meant to do this alone.

I felt very alone through my many deaths, big and small, over the past decade. I’ve gotten much better about asking for help and received support from wonderful therapists and coaches and friends. But it shouldn’t have to be so hard to walk with each other through these cycles.  

For thousands of years, we had guides, elders who had lived through many cycles themselves, to help us on these painful paths. We grieved in community, not just the great deaths, but the little ones too. And yet for social stability we also urged each other to cling to our corpses.

We are in a great cultural bardo at the moment. Those old ways of grieving (and much else) are dead or dying. But nothing solid has yet emerged into its place. We will remain in this liminal space until we turn our attention towards rebirth. To do so, we must first slow down. In that quieter place, we can then explore new ways of grieving, individually and collectively, within our lives and organizations. We can draw on thousands of years of tradition and weave them with the most beautiful threads of modernity, our focus on individual freedom most of all.

Imagine walking in the circle that Rabbi Brous describes here. Not in some grand temple, but somewhere small within the fabric of your modern life. It might be with your spiritual community. Or with your team at the office or the other parents at your kids’ school. You turn and walk the path of the brokenhearted not just when a loved one has physically died, but when you are at the end of a job or company of relationship. Imagine being told over and over by the peers walking towards you: “you are not alone. I will meet your grief with relentless love.” Your pain would not evaporate, but it would sit within a larger container—it would not just be you holding it. Witnessed in that way, maybe you could begin to let go.

I see seeds like this sprouting everywhere. One start-up CEO I support took time away from the existential threats facing the company to carefully create a space in which his team could witness each other in the suffering they felt about the war in Gaza. Another gathered her team during the hectic final weeks of the year to collectively mourn the death of an organizational partnership that had been central to their work. These were not performative exercises out of an HR manual; they were deep and hard and real.

I believe this is some of the most important work we can do in this disenchanted age for ourselves, our organizations, our children. And it all begins with asking that simple question:

What do you need to let die?